#1 WWE to WCW to WWE - Hulk Hogan
Hulk Hogan’s first rise to fame was in the AWA, where he was boosted to huge stardom and selling out houses against champion Nick Bockwinkel. However, Verne Gagne bizarrely seemed to not understand that Hogan was the future of the industry and refused to give him the title.
That, coupled with a fallout over the money rights for his own merchandise, drove Hogan to bolt from the AWA with dates still to work. He promptly signed with WWE, who did recognize that Hogan was the future and helped pushed Hulkamania to the moon.
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That relationship started to sour in 1993 when Hogan made a big return after a year away and pushed his way back up to the top to get the WWE title. However, he and Vince had a major falling out which led to Hogan dropping the belt to Yokozuna before leaving WWE and signing for WCW.
This may have been the biggest loss in WWE history when you consider that the reason we ALL watch wrestling to this day is because of The Hulkster helping to bring it into the mainstream. In WCW, he had another huge falling out with management when Vince Russo went too far in his infamous Bash at the Beach 2000 promo, making Hogan leave for real, suing Russo for defamation of character along the way.
Hogan would eventually find his way back to WWE, once again becoming WWE Champion despite being well past his prime. His return did however give us the fantastic match against The Rock at WrestleMania, so it wasn't all bad.